#------------------------------------------------------------------------------
#$Date: 2019-11-17 14:08:58 +0200 (Sun, 17 Nov 2019) $
#$Revision: 230389 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/05/73/7057347.cif $
#------------------------------------------------------------------------------
#
# This file is available in the Crystallography Open Database (COD),
# http://www.crystallography.net/
#
# All data on this site have been placed in the public domain by the
# contributors.
#
data_7057347
loop_
_publ_author_name
'Bedeković, Nikola'
'Stilinović, Vladimir'
'Friščić, Tomislav'
'Cinčić, Dominik'
_publ_section_title
;
 Comparison of isomericmeta- andpara-diiodotetrafluorobenzene as halogen
 bond donors in crystal engineering
;
_journal_issue                   13
_journal_name_full               'New Journal of Chemistry'
_journal_page_first              10584
_journal_paper_doi               10.1039/C8NJ01368C
_journal_volume                  42
_journal_year                    2018
_chemical_formula_moiety         'C6 F4 I2, 2(C6 H7 N)'
_chemical_formula_sum            'C18 H14 F4 I2 N2'
_chemical_formula_weight         588.11
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2yn'
_space_group_name_H-M_alt        'P 1 21/n 1'
_symmetry_space_group_name_Hall  '-P 2yn'
_symmetry_space_group_name_H-M   'P 1 21/n 1'
_atom_sites_solution_hydrogens   geom
_audit_creation_method           SHELXL-2014/7
_audit_update_record
;
2018-04-25 deposited with the CCDC.
2018-04-27 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 93.572(16)
_cell_angle_gamma                90
_cell_formula_units_Z            2
_cell_length_a                   11.278(2)
_cell_length_b                   5.5135(12)
_cell_length_c                   15.650(3)
_cell_measurement_reflns_used    2208
_cell_measurement_temperature    150(2)
_cell_measurement_theta_max      36.7311
_cell_measurement_theta_min      3.9215
_cell_volume                     971.2(3)
_computing_cell_refinement
;
        CrysAlis RED, Oxford Diffraction Ltd.,
        Version 1.171.32.29 (release 10-06-2008 CrysAlis171 .NET)
        (compiled Jun 10 2008,16:49:55)
;
_computing_data_collection
;
        CrysAlis CCD, Oxford Diffraction Ltd.,
        Version 1.171.32.29 (release 10-06-2008 CrysAlis171 .NET)
        (compiled Jun 10 2008,16:49:55)
;
_computing_data_reduction
;
        CrysAlis RED, Oxford Diffraction Ltd.,
        Version 1.171.32.29 (release 10-06-2008 CrysAlis171 .NET)
        (compiled Jun 10 2008,16:49:55)
;
_computing_molecular_graphics    'MERCURY (C.F. Macrae et al , 2008)'
_computing_publication_material  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      150(2)
_diffrn_measured_fraction_theta_full 0.991
_diffrn_measured_fraction_theta_max 0.992
_diffrn_measurement_device_type
;
Oxford Diffraction Xcalibur CCD
diffractometer
;
_diffrn_measurement_method       'omega scan'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0638
_diffrn_reflns_av_unetI/netI     0.0483
_diffrn_reflns_Laue_measured_fraction_full 0.991
_diffrn_reflns_Laue_measured_fraction_max 0.992
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_k_min       -6
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_number            8829
_diffrn_reflns_point_group_measured_fraction_full 0.991
_diffrn_reflns_point_group_measured_fraction_max 0.992
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         26.995
_diffrn_reflns_theta_min         3.919
_diffrn_source                   'Enhance (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    3.279
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.90041
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlis RED, Oxford Diffraction Ltd.,
Version 1.171.32.29 (release 10-06-2008 CrysAlis171 .NET)
(compiled Jun 10 2008,16:49:55)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    2.011
_exptl_crystal_description       block
_exptl_crystal_F_000             556
_exptl_crystal_size_max          0.61
_exptl_crystal_size_mid          0.55
_exptl_crystal_size_min          0.49
_refine_diff_density_max         0.906
_refine_diff_density_min         -0.710
_refine_diff_density_rms         0.124
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.969
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     119
_refine_ls_number_reflns         2090
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.969
_refine_ls_R_factor_all          0.0458
_refine_ls_R_factor_gt           0.0274
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.0306P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0568
_refine_ls_wR_factor_ref         0.0596
_reflns_Friedel_coverage         0.000
_reflns_number_gt                1657
_reflns_number_total             2090
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            c8nj01368c2.cif
_cod_data_source_block           XIV14
_cod_depositor_comments
'Adding full bibliography for 7057346--7057365.cif.'
_cod_database_code               7057347
_shelx_shelxl_version_number     2014/7
_shelx_space_group_comment
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, -y-1/2, z-1/2'
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
I1 I 0.51437(2) 0.43279(4) 0.16449(2) 0.02337(9) Uani 1 1 d . .
F1 F 0.69140(19) 0.2987(4) 0.01971(14) 0.0315(5) Uani 1 1 d . .
F2 F 0.3205(2) 0.0247(4) 0.10549(14) 0.0332(6) Uani 1 1 d . .
C1 C 0.5854(4) -0.0633(7) 0.3253(3) 0.0292(9) Uani 1 1 d . .
H7 H 0.6636 -0.0898 0.3120 0.035 Uiso 1 1 calc R U
N1 N 0.5018(3) -0.2127(6) 0.2900(2) 0.0307(8) Uani 1 1 d . .
C6 C 0.6644(4) 0.2910(8) 0.4131(3) 0.0433(12) Uani 1 1 d . .
H6 H 0.7384 0.2317 0.3942 0.065 Uiso 1 1 calc R U
H4 H 0.6677 0.2932 0.4746 0.065 Uiso 1 1 calc R U
H5 H 0.6506 0.4523 0.3917 0.065 Uiso 1 1 calc R U
C3 C 0.4484(4) 0.1610(9) 0.3996(3) 0.0372(10) Uani 1 1 d . .
H3 H 0.4293 0.2849 0.4366 0.045 Uiso 1 1 calc R U
C2 C 0.5642(4) 0.1261(7) 0.3798(3) 0.0271(9) Uani 1 1 d . .
C5 C 0.3906(4) -0.1734(9) 0.3111(3) 0.0354(10) Uani 1 1 d . .
H1 H 0.3308 -0.2757 0.2888 0.042 Uiso 1 1 calc R U
C8 C 0.5958(3) 0.1500(7) 0.0115(2) 0.0214(8) Uani 1 1 d . .
C4 C 0.3607(4) 0.0111(9) 0.3642(3) 0.0389(11) Uani 1 1 d . .
H2 H 0.2819 0.0351 0.3763 0.047 Uiso 1 1 calc R U
C9 C 0.4104(3) 0.0165(7) 0.0535(2) 0.0217(8) Uani 1 1 d . .
C7 C 0.5063(3) 0.1718(7) 0.0670(2) 0.0199(8) Uani 1 1 d . .
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
F F 0.0171 0.0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
I I -0.4742 1.8119 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
N1 C1 C2 125.0(4) . .
N1 C1 H7 117.5 . .
C2 C1 H7 117.5 . .
C5 N1 C1 116.4(4) . .
C2 C6 H6 109.5 . .
C2 C6 H4 109.5 . .
H6 C6 H4 109.5 . .
C2 C6 H5 109.5 . .
H6 C6 H5 109.5 . .
H4 C6 H5 109.5 . .
C2 C3 C4 119.6(4) . .
C2 C3 H3 120.2 . .
C4 C3 H3 120.2 . .
C3 C2 C1 116.7(4) . .
C3 C2 C6 122.5(4) . .
C1 C2 C6 120.8(4) . .
N1 C5 C4 122.8(4) . .
N1 C5 H1 118.6 . .
C4 C5 H1 118.6 . .
F1 C8 C9 118.7(3) . 3_655
F1 C8 C7 119.9(3) . .
C9 C8 C7 121.4(3) 3_655 .
C5 C4 C3 119.5(4) . .
C5 C4 H2 120.3 . .
C3 C4 H2 120.3 . .
F2 C9 C8 117.9(3) . 3_655
F2 C9 C7 119.9(3) . .
C8 C9 C7 122.1(3) 3_655 .
C8 C7 C9 116.4(3) . .
C8 C7 I1 121.2(3) . .
C9 C7 I1 122.3(3) . .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
I1 C7 2.094(4) .
F1 C8 1.354(4) .
F2 C9 1.340(4) .
C1 N1 1.346(5) .
C1 C2 1.378(6) .
C1 H7 0.9300 .
N1 C5 1.334(5) .
C6 C2 1.518(6) .
C6 H6 0.9600 .
C6 H4 0.9600 .
C6 H5 0.9600 .
C3 C2 1.375(6) .
C3 C4 1.378(7) .
C3 H3 0.9300 .
C5 C4 1.368(6) .
C5 H1 0.9300 .
C8 C9 1.369(5) 3_655
C8 C7 1.378(5) .
C4 H2 0.9300 .
C9 C8 1.369(5) 3_655
C9 C7 1.385(5) .
loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
C2 C1 N1 C5 -1.0(6) .
C4 C3 C2 C1 -0.8(6) .
C4 C3 C2 C6 177.2(4) .
N1 C1 C2 C3 0.7(6) .
N1 C1 C2 C6 -177.3(4) .
C1 N1 C5 C4 1.4(6) .
N1 C5 C4 C3 -1.6(7) .
C2 C3 C4 C5 1.3(7) .
F1 C8 C7 C9 178.8(3) .
C9 C8 C7 C9 0.2(6) 3_655
F1 C8 C7 I1 0.2(5) .
C9 C8 C7 I1 -178.4(3) 3_655
F2 C9 C7 C8 179.2(3) .
C8 C9 C7 C8 -0.2(6) 3_655
F2 C9 C7 I1 -2.2(5) .
C8 C9 C7 I1 178.4(3) 3_655
